It All Started With That Cup
by ilosttheimpalainthetardis
Summary: Coffeeshop AU Dean's girlfriend is pregnant with a hooker's son, Sam is batting for the other side, and Dean's left alone in a Starbucks on Christmas Day at midnight. As a coffee slides over, a certain Castiel announces it's on the house, and makes a run for it. Dean's curiosity has to be sated, right? Destiel and Sabriel and LOTS OF FLUFF.
1. Chapter 1

**Author's Note: Okay, so a story I based on something I saw on tumblr (ehehe, likely one of the worse in the people who took the prompt), and I hope that you all enjoy! **

**Disclaimer: As much as I love the boys, I don't own them. All credits to Kripke and Co. (If I did, Destiel would be canon. The best I can do as of now is fantasize and write...) **

* * *

**Coffee at Christmas**

You always get the good days, and the bad days, and all those days in between. Just like there are the best days, there are the worst days. And Dean Winchester was having a Worst Day. His girlfriend had announced she was pregnant with another man's child, Sam had just told him that after Jess's death, he turned to bat for the other side, and his friends had all ditched him for their football reunion. They'd forgotten to invite him, for God's sake!

"Lisa. You are with child with another man's- a hooker! You have the kid of a hook- Lisa? Lisa. Gah!" He's really pissed. Sitting in Starbucks on Christmas Day alone was not fun. Not fun at all. Being Dean Winchester, he really wanted to go to a bar, but thinking about Lisa, he didn't want to do that to another woman. He just sat in the coffeeshop, head in his hands. Then a coffee in a mug slid across to him, and it has a dollop of cream on it.

Okay. He has a coffee he didn't order. Looking up, his eyes meet another pair, and he can't help but feel like he was looking into that little creek he grew up next to. It's the exact same shade as the little stream next to their house in Kansas. The stream that he and Sammy would sit by for hours, making up stories about pirates and raids; about everything and anything in between. The creek full of memories that were long gone, but always helped keep him company in those truly lonely nights.

"On the house," the man mumbles, almost inaudibly, and Dean has to strain to hear what he said. The man rushes away too quickly for Dean to say anything else, and all the Winchester can do is sit there and stare at the fast retreating figure. Dean never even got his name, and barely knew anything about him. He watches as a trench coat hurries out the staff exit, and sips his coffee. It's half chocolate, and he can taste some alcohol in it, and he knows that the trench-coated-blue-eyed man knew what he was going through. He finished the drink leisurely, knowing he had nowhere else to be, and left the shop soon after.

* * *

On the other side of the room, a man with half gold eyes watches the man leave. Odd. Since when did Castiel ever give out free drinks? Hell, when did Castiel ever talk to his customers? And when, pray tell, was his brother ever that shy? Castiel had always been socially awkward, but never too shy to even say hello. Gabriel's eyebrows furrowed, and he too left the shop, coat collar turned up against the wind and snow.


	2. Chapter 2

**Author's Note: Hi, I'm back! Special thanks to jasewolff for reading all of my weirdness, and accepting it! So this chapter is just Sam being the little brother, and Crowley appears! So does Jimmy, but Cas doesn't. Sorry, but bear with me until the next chapter, kay?**

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The car was whistling. Whistling. How does a car whistle? Dean sat in the Impala, and he just couldn't hold it in anymore. Grabbing his phone, he dialed Sam's number, and waits for Sam to pick up.

"Hello, Sam Winchester speaking,"

"Okay Sammy boy, where's the whistle?" A muffled giggle escapes on the other end of the line, and Dean feels ready to throttle his little brother.

"Ah... Should we say that it might be... Um... Dean, do you know where your records are?"

"Yeah," Dean did not have a good feeling about this.

"Check each box,"

"Excuse me?"

"Mmmmphlmhphee," is all that Sam can choke out before hanging up, unsuccessfully hiding the guffaws that escape him before he can hang up properly. Dean is ready to deny the entire conversation ever happened. Another _meep_ escapes the whistle, and Dean just cannot, _cannot,_ take the stupid whistling.

Pulling the car over, he opens the drawer by the passenger seat. Pulling out his collection of records covering songs from AC/DC, he paws through the rectangular casings. Finding nothing after a few minutes, he pulls out the box labelled AC/DC-2, and looks through that as well.

After about twenty moments, he finds the source. Sam got a gizmo thingymabob to give out a shrill _meep_ every thirty seconds or so. Opening the door, Dean placed the thing in front of one of the tires. Then he got back in the Impala, and kept driving, smirking when he heard the crisp _crunch_ signalling the end of the unfortunate device.

Heading towards Starbucks, he hopes for a coffee, and maybe to see the mysterious man he saw the other day.

Back in Black starts to blast from something, and Dean fishes his phone out of a pocket, and looks at the number. It's listed as unknown, and he guesses it's a telemarketer.

"Hello?"

"Um, hi, is this..." There's a pause, and the person on the other line fumbles around for something. "Dean Winchester?"

"Yes. Sorry, who is this?"

"I believe you left your card in the Starbucks by Main Street, and I was wondering where your shop was? It doesn't say on the card,"  
"Uh... Sorry?" Dean was confused. The man on the other end of the line had a vaguely British lilt, and seemed to be asking for the address of Dean's garage.

"You're Dean Winchester, the mechanic, right?"

"Yes. You didn't answer my question though. Who are you?"

"I'm Crowley, and I'm a customer. So, where did you say your garage was?"

"It's at 273 Dorower Street, close to Main. Look for the blue sign that says Singer's Auto," This Crowley didn't seem bad, and most publicity was good publicity, right?

"Thanks, mate," Dean hears the click of a phone snapping shut, and looks at his phone like he'd never seen it before. When did customers call him? He was a mechanic, for God's sake! Who called a mechanic with a job?

Stopping at the traffic light, he sees a trench coat hurry past his car on the sidewalk. Dean stares at it for a while, curious, but as a man head towards the trench coat, the head turns, and he sees a very female face looking at the man. So it wasn't the blue-eyed Starbucks server.

Hearing the car behind him honk, he looks up, and sees that the light had changed. Flipping the finger to the man behind him, he sees the man reciprocate, and he drives on to the Starbucks on Main, telling himself he wants to grab a quick coffee before work, but in a little corner of his mind, he knows what he's going for.

The little bell jingles as he opens the door, and he hears Jingle Bells over the speakers, and his mood is improved slightly. Looking around for the man he saw the other day, he wanders over to the end of the line, waiting on the two people in front of him. Looking around, he decides on a vanilla frap, and he's at the front of the line. Looking at the server in front of him, he immediately notices that he doesn't have blue eyes. Or a trench-coat. Or dark hair.

"Good morning, sir, what would you like?" A perky dark haired guy with eyes of the same color greets Dean.

"A vanilla frapuccino, please. The name's Dean," He adds, even though he didn't need to. Business was slow this late in the morning.

"That'll be $12.99," Dean pulls out a $20 bill, and tells him to keep the change.

As he prints a receipt, Dean asks, "Sorry, but," Dean looks at the nametag on the man's shirt. "Jimmy, tell me, does a man in a trench coat work here, blue eyes, dark hair?" As the man taps away at the cashier, he nods and listens to Dean's description.  
"Actually, he might be my brother. He's tall, kinda skinny, really shy, right?"

"Uh, yeah! He's the one with blue eyes,"

"He's Castiel. Why do you want to know?"

"Oh, just saw him around the other day, and got a little curious. Nice guy," The server shrugs, and turns around to make Dean's drink. Since there's not much business, there's only Jimmy working, and Dean heads over to one of the mauve armchairs near the ordering area, waiting for his drink. He mulls the idea of the man with blue eyes, Castiel, over in his head. Those eyes were piercing, almost like they could see right through you. See through everything you ever did, ever saw, ever thought. Everything. His thoughts are interrupted by Jimmy, with his drink.

"Hey, Dean?" Dean looks up from his contemplation, and sees Jimmy with the drink in his hands.

"Oh. Thanks," Dean smiles at Jimmy, and heads out. Driving towards his garage, he sees a nice Bentley outside, but it's an old model. 1920's at least, but a real beauty. Parking his Impala in the driveway, a smaller man in a suit walks up to him.

"You Dean Winchester?" Dean recognizes the voice, the voice with the slightly British lilt to it, the guy who called him to ask about repairs.

"Yeah?"

"You sure? You don't really sound like you're sure," He's cocky, but Dean admires that about him now. He likes people who aren't afraid to voice their opinions.

"You're Crowley, aren't you?" The man nods, and smiles.

"Last I checked. Now, tell me, can you fix my car? It's the Bentley outside," Dean nods respectfully.

"That's a really nice car. 1920's?"

"Actually, yes. 1926,"

"Nice. What's wrong with her?" Dean starts walking inside, gesturing for Crowley to follow him.

"She's whistling," he says flatly. Halfway through his beeline to the fridge to grab a beer, Dean freezes.

"Whistling?" He turns around slowly.

"Yeah. I'm wondering why too,"

"Actually, my car was doing the same thing earlier," Moving towards the fridge again, he offers Crowley a beer.

"Thanks mate,"

"Do you know why it might be whistling?"

"Nope,"

"Do you know a guy called Sam Winchester?"

"Is he related to you?"

"He's my brother,"

"Ah. I see,"

"So you're acquaintances?"

"You could say that,"

"He left a whistling thing on my car," Dean spits the word "thing" out like it's something nasty.

"Oh,"

"Well, let's figure out where he hid it this time, eh?" Dean heads out, and Crowley follows him.

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**Author's Note: Soooo who liked the story? (Whoever liked it please review now. Please?) I'll be off now, but remember, reviews are good for the author, veeeery good. Very very good.**


	3. Chapter 3

**Author's Note: I haven't been updating much on this story, so I'll just add this chapter! Of all of my chapters, this is the crappiest chapter. I'm sorry, and I didn't really have time, so just have this background story on Castiel! Oh, and anyone who gives a review gets an internet cookie! (::)**

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Being one of nine children, Castiel had always been paid attention to. Of course, that was because he was the youngest. His oldest brother, Michael, was the one to give him his first Bible. Lucy, as _she_ was called, gave Castiel his first beer. Gabriel, of course gave him Cas's first sweet. It was sugar. Literally. Gabriel had given Castiel a bowl of had never tasted it before, and had reached his first sugar high. It had taken over three hours for him to reach his sugar low. Even though he was bouncing off of the walls, his family had been amused. He was the baby of the family, what could they do?

Naomi, his second eldest sister, had given Cas his first black eye. Of course, she was in rehab now, so that made sense. She had been on drugs at the time, and Castiel had been in her way. She was now in rehab.

Uriel had given Castiel... nothing. Uriel was actually very quiet, and had never truly been here, on Earth. He was currently in a mental institution, starting from when he was twelve. He believed he was an angel, and referred to everyone as "mud monkeys". It would be alright if not for his violent nature. He tended to hit people when they insulted him, intentionally or not. But the relationship between Castiel and Uriel wasn't bad.

Castiel's computer had been from Anna. It was a birthday present, and now held most of his memories. He carried around everywhere, save work. It held so many memories that he couldn't bear to leave it at home.

Of course, Balthazar was only a year older than Castiel, and ended up getting Cas his first cocktail at Balthazar's 21st birthday.

And Jimmy? Jimmy had always been there for Castiel. They were twins, and did seem to have an empathetic link.

Of course, this was only the siblings. Their mother had died in childbirth with Castiel and Jimmy, but nobody blamed them. It only made them adore the babies of the family more. Their father died when Michael was 25, and Cas and Jimmy had just celebrated their sixteenth birthdays. A heart attack had taken their father, and the three youngest siblings were taken care of by Michael for the few years it took them to become of age. Their family was struck by grief, but like their father always taught them, they moved on. Jimmy and Castiel got a flat together, and moved in one floor above Gabriel.

Michael had left for California by then, taking his family with him. He now lived the kind of apple pie life he'd always wanted. Lucy was different. She had moved to Florida, getting as far away from Michael as she could. Gabe, Castiel and Jimmy lived in New York, and Anna lived in Maryland. Balthazar was in England, living in a dream. Uriel was in a mental institution in Wisconsin, and Naomi was in a jail in Maine. The Novaks had spread all over the country, moving into completely different lives.

Michael was a corporate lawyer, and Lucy was a defensive lawyer. Gabriel owned a sweet shop, and Balthazar was a doctor. Anna worked with charity groups, part time with the Red Cross, and part time as a nurse in her local hospital. Jimmy was the manager of the Starbucks on Main, and Castiel was just a server. Castiel was occasionally a minister in a small church off of 113th Avenue, but it didn't pay well.

Castiel was always the least successful, but the most religious of the nine children. He took after his mother, unobtrusive, but not vacant. Their father used to say that he had an intelligent look in his eyes. Those blue eyes that everyone said looked like either the sea or the sky. Castiel just thought his eyes looked like Listerine mouthwash. Either way, he would likely never get to more than a server in Starbucks.

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Today was Christmas. Of course, it was celebrated everywhere, but Castiel was the only one willing to take this certain shift, so he was alone. Business was slow, and he thought of the eggnog waiting in the fridge at home. Then he saw the man on his phone. Poor guy looked like he needed something to help him cope. Apparently his wife or girlfriend was pregnant with another man's son. Castiel remembers Meg for a moment, and realizes he's not much different from the man. Seeing as there's not much business this late at night, he whips up a hot chocolate with some whiskey in it, topping it with a dollop of whipped cream, carefully placing it upon the foamy exterior of the hot chocolate.

Sliding it across to the man, he finds that after flicking his eyes up to meet the other man's, he can't seem to meet them again. Despite his odd habit of staring at random people, Castiel seems a bit lost.

"On the house," he manages to mumble, and scoots off, grabbing his trench coat and rushing back to his apartment. Even though he forgot to clock out, he knows that Jimmy will do it for him, making up the time. He's done it for Jimmy enough to know that for once Jimmy can cover for him.

Pulling his coat tight to fend off the cold, he nearly slips on a frozen puddle right outside his door, and unlocks the apartment door. Hearing the sudden clang behind him that announced the closing of the door, he sighs in relief. Castiel hated confrontations, and did his best to avoid them.

Walking upstairs, he gets to the sixth floor, taking another key off of the keychain that Gabriel gave him for his twentieth birthday, a blue one with an angel dangling off of it.

"An angel for an angel, eh?" Gabriel had said when he had given it to him. Castiel kept it as a reminder to have faith. Unlocking the door, he wandered into his room. Plopping himself into bed, Castiel doesn't even bother to change. Trying to sleep, he can't seem to get a certain shade of green out of his head.

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**Author's Note: How was it? Horrible? Good? Not bad? Then tell me! There's a box down there where you can review... Yup! Thanks! :)**


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